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Amphibine H
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Cyclopeptide Alkaloid
| Canonical Smiles | COc1ccc2cc1/C=C\NC(=O)C(NC(=O)C1C(O2)CCN1C(=O)C(C(C)C)NC(=O)C(N(C)C)C)Cc1ccccc1 |
|---|---|
| InChI | InChI=1S/C33H43N5O6/c1-20(2)28(36-30(39)21(3)37(4)5)33(42)38-17-15-27-29(38)32(41)35-25(18-22-10-8-7-9-11-22)31(40)34-16-14-23-19-24(44-27)12-13-26(23)43-6/h7-14,16,19-21,25,27-29H,15,17-18H2,1-6H3,(H,34,40)(H,35,41)(H,36,39)/b16-14- |
| InChIKey | KLYKBXVHBJWDJF-PEZBUJJGSA-N |
| Formula | C33H43N5O6 |
| HBA | 7 |
| HBD | 3 |
| MW | 605.74 |
| Rotatable Bonds | 8 |
| TPSA | 129.31 |
| LogP | 1.96 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 605.32 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ziziphus spina-christi | Rhamnaceae | Plantae | 264981 |
Showing of synonyms
Amphibine H
N-(1-{10-benzyl-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.3.1.0^{3,7}]nonadeca-1(18),13,15(19),16-tetraen-6-yl}-3-methyl-1-oxobutan-2-yl)-2-(dimethylamino)propanamide
N-[1-[(13E)-10-benzyl-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo[13.3.1.03,7]nonadeca-1(19),13,15,17-tetraen-6-yl]-3-methyl-1-oxobutan-2-yl]-2-(dimethylamino)propanamide
N-(1-((13E)-10-benzyl-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo(13.3.1.03,7)nonadeca-1(19),13,15,17-tetraen-6-yl)-3-methyl-1-oxobutan-2-yl)-2-(dimethylamino)propanamide
N-(1-(10-benzyl-16-methoxy-8,11-dioxo-2-oxa-6,9,12-triazatricyclo(13.3.1.0^(3,7))nonadeca-1(18),13,15(19),16-tetraen-6-yl)-3-methyl-1-oxobutan-2-yl)-2-(dimethylamino)propanamide
Klykbxvhbjwdjf-pezbujjgsa-n
CHEBI:168861
2-(Dimethylamino)-N-[2-methyl-1-[[3,3a,12,13,14,15,16,16a-octahydro-8-methoxy-13,16-dioxo-14-(phenylmethyl)-5,9-metheno-9H-pyrrolo[3,2-b][1,5,8]oxadiazacyclopentadecin-1(2H)-yl]carbonyl]propyl]propanamide, 9CI
- Abdel-galil F, El-Jissry M. (1991). Cyclopeptide alkaloids from Zizyphus spina-christi. Phytochemistry, 1991, 30(4), 1348-1349. [View]
No compound-protein relationship available.
SMILES: c1ccccc1CC(NC(=O)C(C23)NCC2)C(=O)NC=Cc4cc(O3)ccc4
Level: 1
Mol. Weight: 605.74 g/mol
SMILES: C1CNC(C12)C(=O)NCC(=O)NC=Cc3cc(O2)ccc3
Level: 0
Mol. Weight: 605.74 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 605.74 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.98
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.960
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 13.96
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.890
- Plasma Protein Binding
- 34.19
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.370
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.020
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.300
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.080
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -25644.350
- Rat (Acute)
- 3.130
- Rat (Chronic Oral)
- 1.680
- Fathead Minnow
- 49.970
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 205.830
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.620
- Log(P)
- 1.97
- Log S
- -2.95
- Log(Vapor Pressure)
- -11.25
- Melting Point
- 209.81
- pKa Acid
- 8.14
- pKa Basic
- 7.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.9730 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.9145 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.9033 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8986 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8971 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8803 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8780 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8776 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.8774 |
| Pol protein | Q000H7 | Q000H7_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8130 |
| Antitumor antibiotic C-1027 apoprotein | Q06110 | CAGA_STRGL | Streptomyces globisporus | 3 | 0.8030 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7959 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7687 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7672 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7668 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7630 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7544 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 3 | 0.7472 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 2 | 0.7452 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7426 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7413 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7412 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7384 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7369 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7339 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7311 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7310 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7302 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7279 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7251 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7244 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7243 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7238 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7228 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7224 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7221 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 2 | 0.7207 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7174 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7166 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 2 | 0.7148 |
| Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 2 | 0.7147 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7145 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7136 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7113 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7085 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 4 | 0.7084 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7073 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7046 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7041 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7041 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7021 |
| Carnitine O-palmitoyltransferase 2, mitochondrial | P18886 | CPT2_RAT | Rattus norvegicus | 3 | 0.7005 |